


Headcanons

by Pineapplemoon



Series: I'm a Book Half Unread [17]
Category: Gilmore Girls
Genre: And anxiety, Developing Relationship, Father-Son Relationship, First Time, Gen, Headcanon, M/M, What-If, jess has adhd
Language: English
Status: In-Progress
Published: 2019-10-16
Updated: 2020-07-25
Packaged: 2020-12-17 07:40:25
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 9
Words: 2,666
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21050732
Author URL: https://archiveofourown.org/users/Pineapplemoon/pseuds/Pineapplemoon
Summary: Headcanons and other asks I receive over on tumblr for this series.





	1. Chapter 1

**Author's Note:**

> I figured I would put these in a place that's easy for others to find. I'm going to be leaving on Oct. 20th for two and a half weeks. I'm not going to be able to get the next part out before I leave but I didn't want to leave everyone hanging so here is some bonus content that I hope will tide everyone over until I get back.
> 
> This was an ask I received on tumblr a while back. If anybody wants to know any headcanons, you can leave them on my tumblr (Pineapplem00n) or leave something in the comments here.

**Ooh, headcanons for Ollie with Jess? Like what are they like around one another? Who's softer? Who's more innocent? How does Ollie deal with Jess's anxiety? -Anon on tumblr  
**

Literally the first thing that popped into my head was something like this:

Rory: “So who’s the big spoon and who’s the little spoon?”

Jess: “I’m a knife!”

Ollie, somewhere in the background: “He’s the little spoon.”

As silly as that is, that’s literally the best description for those two. Jess likes to act all tough and a real James Dean type, but in reality he’s just a big softy.

Jess’ idea of a good time is staying in and expanding Ollie’s movie knowledge to include more and more abscure, horrible 80s movies imaginable. (i.e. Mac and Me)

Oliver’s the mother hen of the two. He’s constantly checking in to make sure Jess is good eating and comfort wise. Jess is used to not telling people his needs since there usually wasn’t anyone to tell, so unless Oliver outright asks Jess “Are you hungry? Are you thirsty? What do _ you _ want?”. Oliver gets Jess to advocate for himself more.

Jess gets Oliver outside his comfort zone more in regards to being more himself. Oliver grew up being told to act a certain way, dress a certain way, ect. much like Lorelai’s upbringing, so he’s in a way showing Oliver “See, look at Lorelai. There is more to life than worrying about what your parents will think.” Jess has a very YOLO outlook on life. *Cue the Aladdin “I will show you the world” ride on a carpet scene with Jess and Ollie*

Jess is less of the “less innocent” one and more “had his innocence ripped away”. Living with Liz and in New York forced Jess to grow up way too fast. Being the child and yet doing your mother’s taxes, budgeting the money for food, rent, clothing, ect. would do that to you. On a scale, he’s tipped from “realistic” to “cynical” at a way too young age. Luke and Oliver tend to team up and try and get Jess to be just a little bit more whimsical, and dream more.

Oliver grew up very sheltered. It’s not a fault of his own, he comes from a family of old money, but that tends to skew his vision of the world. When Jess took Ollie to New York and showed him downtown or as Jess called it “the real New York” it was a real eye opener for him. Seeing how Jess and so many other people live was like a splash of cold water.

Jess is slow to trust and open up, so he’s downplayed a lot of his anxiety. Luke, and by extension Lorelai, are the only two that know the full extent of his anxiety. Oliver isn’t oblivious or an idiot though and has suspicions about how bad it actually can get, but doesn’t want to overstep the mark so he won’t bring it up unless Jess is the one to bring it up. He’s done research on his own though on ways to cope, and can recognize now when Jess gets a checked out look on his face or starts to fidget more than normal that that’s a sign to switch to a conversation that’s comfortable for Jess or even just spend quiet time letting Jess read a book while he works on his laptop. Jess is a bit like a cat in the regard that he from time to time needs space, but also likes for both of them to be in the same room doing their own things silently. He likes company, but doesn’t always want to talk. He doesn’t want to be antisocial, but sometimes he gets super stressed out talking to people at school all day and just needs the time to decompress.

They have a good balance of Jess being an introvert and Oliver being an extrovert. Oliver pulls Jess out of his shell and Jess makes sure Oliver stops to breath between sentences.

Thank you so much for this amazing ask! It was a great writing exercise for me and I will definitely be saving it in my notes to look back on while writing.


	2. Jess' ADHD

**Headcanons for Jess' ADHD? Like, how does he handle it? Do his teachers help at all? How does Oliver help him?** **-Anon on tumblr**

-Jess doesn’t get the hyper side of things too much, but he does get the mood swings involved with ADHD, which he has started to recognize and is working on not snapping at people as his go to response.

-It’s a hit and miss with the teachers. A few have recognized the signs and have learned that as long as they make clear deadlines and expectations, Jess will work at his own pace to get things done. Others have figured out that no matter how much he does his homework and aces tests, he will almost never volunteer or raise his hand to answer a question or participate unless they specifically ask him something. He has to be coaxed into being active in the class. Most just leave him alone and let him work at his own pace, which is ahead of the class.

-If a class is free to move around the room and chat to work on projects, he usually gets a pass to go work in the library where it’s quiet and he can focus better.

-Jess tunnel visions A LOT. If he’s completely focused on one thing, you can be having a direct conversation with him and he won’t notice. The best example is when Dean came over for the first time and Jess was reading with his music on. He wasn’t ignoring Dean to be funny, he was just focused on his book and legitimately didn’t notice Dean standing there until Dean was literally yelling at him.

-AND THE LAUNDRY! The amount of times Luke has had to do his laundry because Jess starts to, leaves wet clothes in the washer for hours, and then Luke finds it and ends up doing it is too many.

-Oliver knows to call his name or get his attention before asking a question, otherwise it won’t process for Jess.

-Also double check about plans. Jess forgets sometimes or will lose track of time and one hour can turn into 6 and then all of a sudden Jess will blink and realize he spent 6 hours reading a book at the bridge.

**Notes for the Chapter:**

> Please feel free to ask more on here or on tumblr. My handle over there is Pineapplem00n


	3. The 'I love yous'

**Notes for the Chapter:**

> I just got back from vacation so I'll get back to writing again. For now I'll post a few asks I got on Tumblr while I was away and get the next installment out as soon as I can. If you don't see your ask right away, don't worry, I'll get to it soon. Some I had to think over a little more.

**I’ve just finished all your works with Jess and let me say, amazing character representation!!! 👏🏼👏🏼 also, is when do you think Jess knew that he was in love with Oliver? (Even if it’s not directly said, you can tell indirectly that they are, especially with the last meat part) Have they said it yet, I can’t remember if I saw it or not, and if they didn’t, who said it first? Where? When? -Anon on tumblr  
**

Thank you so much!! I had it implied that oliver said it first at the end of Ya Got Trouble, but Jess never verbally said it back. I think he has enough trouble saying it to Luke, it's nearly impossible for him to say it to someone that's not a family member. (I am going to address it more down the line, don’t worry)

Oliver only said the big three words that one time because emotions were high with his father just finding out about their relationship and he didn't mean to let it slip.

I think Jess realized their relationship meant more to him than any other relationship fairly early on. I would put it a little after the New York fiasco, after they made up. In the past if he got in a fight with someone he’s dating he would play the avoidance game, but it was eye opening for him to realize that he wanted to try and fix things, even if that's the harder path to take.

I hope that answers everything and I might make some tweaks to it later. I'm on vacation at the moment and only have my phone to work off of and spotty wifi service.

**Notes for the Chapter:**

> As always, my tumblr is Pineapplem00n


	4. Oliver's appearance

**What does Oliver look like in your mind when writing him? Cause whenever I read your works I picture the Oliver from How to Get Away With Murder 👀👀** **-Anon on Tumblr**

I imagine about Jess’ height and build, maybe a bit taller with a tiny bit more muscle. Blond hair that lays flat and no product in it. It’s on the shorter side, but not close crop or a buzz cut. His everyday clothes are like smart casual ish. He wears jeans, but more button ups than t-shirts, although when the weather gets hotter he goes for shorts and t-shirts with those brown cloth flip flops (I don’t know enough about fashion if those have a special name lol).

I hope that helps 😁 I try not to get too detailed in the fic so people can imagine him how they want, but this is usually what I have in mind when writing. (I barely watched how to get away with murder so the name is just a coincidence. I chose the name from Arrow’s Oliver Queen and the last name from Manifest’s Olive Stone.)

**Notes for the Chapter:**

> My tumblr is Pineapplem00n


	5. Jess and Oliver's first time

**Notes for the Chapter:**

> Sorry this is late, but I wanted to take my time thinking it through. Hope you enjoy!

**Can we can a head cannon for Jess and Oliver’s first time??? 👀👀 I mean; not like too much into details, but yenno, when, where, how it happened, how Jess felt, and how Oliver felt? -Anon on tumblr**

It happened at some point when Luke was spending the night in New York with Nicole, so Jess and Oliver had the apartment to themselves. It wasn’t planned, and was Oliver’s idea. Jess was a little more hesitant and was nervous that he had been unknowingly pressuring Oliver into it, but Oliver assured him that it was his idea.

There was a lot of awkward fumbling before the two kind of figured out what they were doing. Oliver had never slept with anyone and despite the playboyish air Jess likes to give off when he references his time before moving to Stars Hollow, he had only slept with one girlfriend when he had first turned sixteen. She had been older, and not to be crude, but was a bit of a bang em and leave em type. She left right after they were done and broke up with him the next day.

Jess wished that he had waited for this to be his first time instead, but was glad that he was able to in a way give Oliver a better first time experience then he had.

Oliver was relieved almost that they got it out of the way. Kids at school and on tv had always built it up to be this big, huge milestone and he was nervous about getting it perfect. It wasn’t perfect, but they had fun and were laughing when they were still trying to get the mechanics down as it were. In a way, it was perfect, just their version of perfect.


	6. What if

**Notes for the Chapter:**

> You asked a really good question that had me thinking and I hope this answer measures up.

**Head cannon if Jess ever lashed out at Oliver after the NY fiasco? - friendlyreader348 on Ao3**

I think Oliver would break up with him right there. He has enough self respect that he doesn’t deserve to be treated that way and sticks up for himself. Jess is already on thin ice after their fight the night when they got back from New York, and the only reason Oliver gave him a second chance was because Jess showed up, apologized like crazy, and admitted the things he said while drunk were way out of line. If Jess ever lashed out again, Oliver would see it as a pattern and wouldn’t want to be in a relationship where Jess puts him down verbally and then gets away with it every time he apologizes.

**Notes for the Chapter:**

> Tumblr is Pineapplem00n


	7. Post prom conversation

**Canon for how Oliver felt/thought after the fight and the conversation with Jess from prom? 👀🤗 also what happened with his dad after the breakup and Jess bringing him home drunk? 😬🤗 -tumblr anon**

Oliver felt relieved, if a little sad, about getting closure after prom. He had felt horrible for what he said and did while drunk at the party, but was too scared to approach Jess about it. A little part of him did want to get back together, but agreed with Jess that it’s for the best that they part ways. Jess may have forgiven him for yelling that he hated him and throwing the stuff with Liz in his face, but that’s something Oliver is going to regret and will haunt him for a long time. He doesn’t believe that him being drunk is an excuse, because he knows it came from somewhere. It didn’t just appear out of no where. Jess was right that they were saying things purposely that they knew would hurt each other the most.

As for what happened between Oliver and his father after Jess left, I’m keeping that a secret for now. I debated adding it in the prom conversation (that’s partly why it took so long to update) but ultimately decided against it when I just couldn’t find a good place for it. Not in the next part, but in the part after that is probably when it will get addressed, maybe one after that, I’m not entirely sure, but it will for sure get addressed because stuff did happen. I don’t want to spoil it but all I will say is that Jess was discussed.

Oliver is for sure coming back, because unlike certain other writers/creators of a certain show, I believe characters should still have a life outside of dating main characters. All of his character progression does not revolve around Jess, and I like seeing characters grow outside of their relationships because that’s how it works in real life.

**Notes for the Chapter:**

> Tumblr is badwolfchild


	8. Jess' depression at college

**Any hcs for how Jess’ depression will be when he goes to college -Confused-sagittarious on tumblr  
**

Not as bad as one might think. Rory is nearby and Friday, as usual, is dinner at the Gilmore’s so he can see Lorelai, Richard, and Emily.

It will take a little adjusting to get used to Luke not being right there all the time, but phone calls and weekend trips to Stars Hollow with Rory brighten his day. (Not that he would ever admit it out loud lol)


	9. Update + General questions

**I recently found your Gilmore Girls series on AO3 and I love it so so much. I just have a couple questions if you don't mind. Are you going to continue it? If so what are some ideas that you might have that you want to share? What is in the envelope Jess gets from his father? I love Luke and Jess's relationship on the show and when I came across your series, I couldn't stop reading. You're an amazing writer!! -tumblr anon**

I really really want to, I just got stuck and writing my Witcher fic was easier and flowing better. Sometimes I have to take small breaks from writing one fandom and switch to a different one, otherwise I get bored and it shows in my writing that I was just bsing to get words on a page.

First off, the envelope will be explained in the next chapter that I’m halfway done with, so I’ll try and finish so I can post that. 

Some ideas I have floating around is Oliver will still be a reoccurring character and I’ll dive more into his family life, and him and Jess getting to know each other as friends, not boyfriends.

Luke and Jess are such an underrated underwritten relationship that I love exploring. Jess in general was underwritten. I wish we could have gotten more about his life before moving to Stars Hollow. He had the most character growth in the entire series and we didn’t even get to see half of it!

Okay, rant over. Anyway, thank you for all the compliments, they make me so happy and remotivate me to write more!


End file.
